Windsor Vacation Packages
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Top Holiday Package Deals in Windsor
Price found within the past 48 hours. Click for updated prices.
Ellipse Executive Apartments
Midrand
CA $2,064
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Johannesburg (JNB)
9/10 Wonderful! (20 reviews)
Ellipse has a fantastic location right next to Mall of Africa, and the aparthotel itself was very nice, but poor internal communication significantly hurt the experience. Check-in was confusing since I received no prior instructions, and despite arriving after the 3:00 PM check-in time, I had to wait in the hallway while housekeeping finished up. Later, I was granted an extra hour for late checkout (12:00 PM) because I was unwell, but management failed to notify staff. Housekeeping knocked at 11:00 AM and again at 11:30 AM, completely disrupting my rest. On top of that, the 6-digit access code repeatedly malfunctioned when trying to exit the building and parking areas. It’s a great property, but management urgently needs a centralized communication system.
Reviewed on Aug 22, 2026
Tuningi Safari Lodge
CA $15,421
per person
Nov 9 - Nov 15
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Johannesburg (JNB)
10/10 Exceptional! (2 reviews)
This place is absolutely remarkable with a staff that takes it up a level. Mgmt. team Heidi and Michelle were excellent and always upbeat.
Andres our guide did his absolute best to track everyone of the big five even in the rainy weather. Even with rainy weather for 3 of our 4 days we got to see 4 of the 5.
Reviewed on Dec 15, 2019
The Residence Boutique Hotel
Houghton Estate
CA $3,215
per person
Nov 9 - Nov 15
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Johannesburg (JNB)
9.8/10 Exceptional! (308 reviews)
Never have been disappointed staying here.
Great staff, excellent food, great piano player, comfortable rooms
Reviewed on Apr 28, 2026
54 On Bath
Rosebank
CA $2,426
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Johannesburg (JNB)
9.6/10 Exceptional! (265 reviews)
Staff were so kind & accommodating. They were always available to help with anything you needed. The breakfast was amazing as were all the meals. I will definitely stay there again the next time I visit. Also a great perk being attached to the mall.
Reviewed on Aug 26, 2026
Where to stay in Windsor
Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Sandton
4 out of top 10 points of interest in this area
A noteworthy feature of Sandton is its popular shops. While you're in town, be sure to stop and check out Nelson Mandela Square and Sandton City Mall.
Rosebank
1 out of top 10 points of interest in this area
Rosebank is known for its ample dining options, and you can make a stop by Rosebank Mall and The Zone @ Rosebank Shopping Center while in the area.
O.R. Tambo
1 out of top 10 points of interest in this area
While visiting O.R. Tambo, you might make a stop by sights like International Terminal Duty Free Mall and Emperors Palace Casino.
Midrand
1 out of top 10 points of interest in this area
You'll enjoy the gardens and spas in Midrand. You might want to make time for a stop at Mall of Africa or Kyalami Racetrack.
Randburg
Unique features of Randburg include the golf courses and gardens. Make a stop by Emmarentia Dam or Cresta Shopping Centre while you're exploring the area.
Windsor Hotel Deals
City Lodge Hotel at OR Tambo International Airport
Above Multi-Storey Parkade 2, Level 5 Kempton Park Gauteng
CA $205
CA $236 total
Sep 23 - Sep 24
includes taxes & fees
Southern Sun O.R Tambo
Airport Grounds, Jones Road, / Kempton Park Gauteng
Fully refundableReserve now, pay when you stay
CA $180
CA $206 total
Sep 26 - Sep 27
includes taxes & fees
Sandton Sun & Towers
Cnr. Fith And Alice Streets Johannesburg Gauteng
Fully refundableReserve now, pay when you stay
CA $278
CA $324 total
Sep 12 - Sep 13
includes taxes & fees
9.2/10 Wonderful! (632 reviews)
"This Hotel along with staff is top notch very well appointed rooms staff fantastic highly recommend"
Reviewed on Aug 24, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Windsor vacation package cost?
Browse and book everything in one place with our Windsor vacation packages, which start from just CA $2,064. Select the hotels and flights that match your travel plans. Then, add on a few tours or experiences for an incredible getaway.
How do I get a cheap travel package to Windsor?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you dollars too. A Windsor vacation package makes it a cinch to arrange the ideal trip. With more than 550 airlines around the world to select from, finding flights that suit your schedule will be no sweat. Not only that, we have over 1,000,000 hotels globally to pick from. Now that's what we call choice. Whatever your budget, Expedia can show you the world.
Where should I stay in Windsor?
Stay where the action happens. Many travelers book hotels within easy reach of top attractions, such as Cresta Shopping Centre, Randpark Golf Club and Johannesburg Eye Hospital.
What are the top hotels in Windsor?
Get your trip off to a fantastic start by reserving a room at Isabel's Guesthouse. It's one of most sought-after hotels in Windsor. Another welcoming option is Khamanzi Lodge And Tours.
How far in advance should I book my Windsor vacation?
Search Expedia to compare international flights as soon as you've got your travel dates. In many cases, you can purchase a seat up to 12 months before departure. If you can't find your preferred carrier, or you've left things to the last minute, don't stress. The lowest prices to Windsor sometimes occur just weeks before departure.
What does an Expedia Windsor travel package include?
From airfares and hotels to car rentals, Expedia can help you create a Windsor package that's right for you. Heading away for a while? Look into a rental car, flight and hotel bundle. If your break is short, a hotel and airfare deal could be what you're after. Tours and activities can be added once you've made your booking. Our vacation packages make it a cinch to save and plan.
What should I know before booking a Windsor travel package?
You can save a tidy sum by combining your hotels, airfares and rental cars. Once you've created your package, you can add on things like activities or sightseeing tours. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Windsor Expedia vacation package?
Expedia has access to more than 550 partner airlines globally, so you certainly can. Simply choose your preferred air carrier and put together your ideal Windsor escape.
If I'm not able to travel, can I cancel my Windsor vacation package?
We totally get that life doesn't always go according to plan. If you've locked in a Windsor vacation package and have to amend or cancel it, we can help. We recommend taking a look at our Customer Service Portal first for information. But generally speaking, if you've taken out your package within 24 hours, you may be able to cancel and rebook for free. If it's more than 24 hours, your hotel, airline or car rental company may impose a charge.
Things to do
From Johannesburg: Rhino & Lion Safari and Wonder Cave Tour
CA $164
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.